US3855200A
Expired / Lapsed
US
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Process for preparing 8-hydroxyerthromycin a and intermediates therefor
Assignee: Polish Academy of Sciences
•
Filing: 1973-04-23
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Granted: 1974-12-17
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Expires: 1993-04-23
Abstract
Abstract 8-Hydroxyerythromycin A is prepared from 8,9-anhydroerythromycin A 6,9-hemiketal in two steps.
Inventors
- 👤 K Krowicki
- 👤 A Zamojski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:53
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
49 words
THE PROCESS WHICH CONSISTING ESSENTIALLY OF REACTING 8,9ANHYDROERYTHROMYCIN A 6,9-HEMIKETAL WITH MCHLOROPERBENZOIC ACID IN A MIXTURE OF ETHYL ACETATE AND WATER TO FORM THE N-OXIDE OF 8-HYDROXYERYTHROMYCIN A 6,9HEMIKETAL AND THEN REDUCING SAID N-OXIDE WITH HYDROGEN IN THE PRESENCE OF A PLATINUM OR PALLADIUM CATALYST TO PRODUCE 8-HYDROXYERYTHROMYCIN A.
Claim 2
Dependent Claim
49 words
THE PROCESS WHICH CONSISTING ESSENTIALLY OF REACTING 8,9ANHYDROERYTHROMYCIN A 6,9-HEMIKETAL WITH MCHLOROPERBENZOIC ACID IN A MIXTURE OF ETHYL ACETATE AND WATER TO FORM THE N-OXIDE OF 8-HYDROXYERYTHROMYCIN A 6,9HEMIKETAL AND THEN REDUCING SAID N-OXIDE WITH HYDROGEN IN THE PRESENCE OF A PLATINUM OR PALLADIUM CATALYST TO PRODUCE 8-HYDROXYERYTHROMYCIN A.
Claim 3
Dependent Claim
56 words
The process which consisting essentially of reacting 8,9-anhydroerythromycin A 6,9-hemiketal with m-chloroperbenzoic acid in a C1-C4 alkanol to form the N-oxide of 8-hydroxyerythromycin A C1-C4 alkyl-6,9-ketal, reducing said N-oxide with hydrogen in the presence of a platinum or palladium catalyst, and subjecting the product of the reduction to an mild acid hydrolysis to produce 8-hydroxyerythromycin A.
Claim 4
Dependent Claim
56 words
The process which consisting essentially of reacting 8,9-anhydroerythromycin A 6,9-hemiketal with m-chloroperbenzoic acid in a C1-C4 alkanol to form the N-oxide of 8-hydroxyerythromycin A C1-C4 alkyl-6,9-ketal, reducing said N-oxide with hydrogen in the presence of a platinum or palladium catalyst, and subjecting the product of the reduction to an mild acid hydrolysis to produce 8-hydroxyerythromycin A.
Claim 5
Dependent Claim
62 words
The process which consisting essentially of reacting 8,9-anhydroerythromycin A 6,9-hemiketal with m-chloroperbenzoic acid in an anhydrous aprotic solvent to form the N-oxide of 8-hydroxyerythromycin A 6911-spiroketal, reducing said N-oxide with hydrogen in the presence of a platinum or palladium catalyst to the 6911-spiroketal of 8-hydroxyerythromycin A, and subjecting the product of the reduction to an mild acid hydrolysis to produce 8-hydroxyerythromycin A.
Claim 6
Dependent Claim
62 words
The process which consisting essentially of reacting 8,9-anhydroerythromycin A 6,9-hemiketal with m-chloroperbenzoic acid in an anhydrous aprotic solvent to form the N-oxide of 8-hydroxyerythromycin A 6911-spiroketal, reducing said N-oxide with hydrogen in the presence of a platinum or palladium catalyst to the 6911-spiroketal of 8-hydroxyerythromycin A, and subjecting the product of the reduction to an mild acid hydrolysis to produce 8-hydroxyerythromycin A.
Claim 7
Dependent Claim
20 words
The process of claim 2 in which the C1-C4 alkanol is methanol and the ketal produced is 8-hydroxyerythromycin A methyl-6,9-ketal.
Claim 8
Dependent Claim
6 words
The N-oxide of 8-hydroxyerythromycin A 6911-spiroketal.
Claim 9
Dependent Claim
6 words
The N-oxide of 8-hydroxyerythromycin A 6911-spiroketal.
Claim 10
Dependent Claim
8 words
The N-oxide of an 8-hydroxyerythromycin A C1-C4 akyl-6,9-ketal.
Claim 11
Dependent Claim
8 words
The N-oxide of an 8-hydroxyerythromycin A C1-C4 akyl-6,9-ketal.
Claim 12
Dependent Claim
15 words
A compound according to claim 6, said compound being the N-oxide of 8-hydroxyerythromycin A methyl-6,9-ketal.
Claim 13
Dependent Claim
6 words
A 2''-C2-C4 alkanoate of 8-hydroxyerythromycin A.
Claim 14
Dependent Claim
6 words
A 2''-C2-C4 alkanoate of 8-hydroxyerythromycin A.
Claim 15
Dependent Claim
14 words
A compound according to claim 8 said compound being the 2''-acetate of 8-hydroxyerythromycin A.
Claim 16
Dependent Claim
4 words
The 6911-spiroketal of 8-hydroxyerythromycin.
Claim 17
Dependent Claim
4 words
The 6911-spiroketal of 8-hydroxyerythromycin.
Claim 18
Dependent Claim
6 words
A C1-C4 alkyl-6,9-ketal of 8-hydroxyerythromycin A.
Claim 19
Dependent Claim
6 words
A C1-C4 alkyl-6,9-ketal of 8-hydroxyerythromycin A.
Claim 20
Dependent Claim
14 words
A compound according to claim 11, said compound being the methyl-6,9-ketal of 8-hydroxyerythromycin A.
References Cited (Backward Citations)
US3674337A
Cited
US3736313A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-16 | 1978-06-17 | 1978-12-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-16 | 1982-06-17 | 1982-12-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-16 | 1986-06-17 | 1986-12-17 | $7700.00 | Window Closed / Lapsed |